Synthesis
Example 1A Synthesis of tert-butyl 4-((tolylenesulfonyloxy)methyl)piperidine-1-carboxylate: N-BOC-4-piperidine methanol (10 g, 46.5 mmol) and triethylamine (5.64 g, 55.8 mmol) were dissolved in dichloromethane (100 mL) under nitrogen protection and cooled to 0°C. Subsequently, p-toluenesulfonyl chloride (9.73 g, 51.2 mmol) and 4-dimethylaminopyridine (1.13 g, 9.3 mmol) were slowly added to the solution. The reaction mixture was stirred at 17°C for 2 hours. After completion of the reaction, the reaction was quenched by the addition of water (100 mL). The aqueous layer was extracted with dichloromethane (100 mL x 2). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. Purification by column chromatography afforded 1-N-Boc-4-(4-methylbenzenesulfonyl oxymethyl)piperidine (17 g, 99% yield) as a white solid.LCMS (ESI) m/z: 370 (M + 1).
References
[1] Patent: US2017/29430, 2017, A1. Location in patent: Paragraph 0255
[2] Patent: CN105315267, 2016, A. Location in patent: Paragraph 0033; 0049
[3] Patent: WO2008/42282, 2008, A2. Location in patent: Page/Page column 107-108; 168-169; 210-211
[4] Patent: WO2012/168349, 2012, A1. Location in patent: Page/Page column 37
[5] Patent: US2013/34504, 2013, A1. Location in patent: Paragraph 0147; 0148; 0149
